I believe not having enough money is a great lesson in life.

Buying and then realizing you are short on funds to do repairs and remodeling teaches us to be frugal. If you pass through the storm your habits are fine tuned and efficient.

Only,

If you continue and become too frugal, Do you actually harm your progress.

Ever met the personality who just launches ideas, somehow avoiding the details along the way until the project pays out great profits. I admire these people, I know sometimes they have a person behind the scenes covering for them, still, they are more likely to take chances and do well.

I think I settle into a pattern, and from time to time I need to remind myself to take risks.

My question is, do you have habits which made you successful but could actually be causing you harm now?

During a down swing in the real estate market I found three properties to buy on the same day. I make three low ball offers. And by misfortune, all three were accepted.

I had the money to do what was necessary to get all three apartment properties rented out and in acceptable condition. But the City and County Departments were hurting for funds due to the drop in prices/taxes.

I was preyed on like hungry wolfs after a lonely fox in the dead of winter. Everyone wanted my blood. When asked why they were so mean and petty, their response, "IF you don't have the money to be a landlords then you should be in the business".

I went after the County Assessor who over taxed property owners and kept their proceeds for an average of 18 months during the appeals process, earning the County $26,000,000 in interest. The settlement, pay back the lost interest to any owner who could prove the were over taxed. They County paid out only $13,000,000. SO their fraud was worth the effort.

there are things you want to do and things you need to do.

knowing the difference is the key

You absolutely do not need money to make it in this business. When I was young and bootstrapping, things got done and I had to use maximum creativity to make things happen.